Certain derivatives of s-triazolo [4, 3-a]-pyridine



United States Patent 3,050,525 CERTAIN DERIVATIVES OF s-TRKAZOLO [4,3-a]-PYRIDINE John B. Bicking, 622 Salford Ave, Lansdale, Pa. N0 Drawing. Filed Dec. 14, 1960, Ser. No. 75,668 6 Claims. (Cl. 260296) This invention relates to S-Substituted pyrido (2.1-c)-striazoles and particularly to those having an unsubstituted or an acyl substituted amino lower alkyl group at the 3- position.

The 3-substituted pyrido (2.1-c)-s-triazoles of the present invention can be derived from the process set forth in my U.S. Patent 2,917,511 and comprise compounds having the following formula:

wherein R can be a lower alkyl up to four canbons, preferably methyl and ethyl and R is hydrogen or acyl, preferably benzoyl or the residue of a lower aliphatic acid having up to 4 carbon atoms.

The compounds of the present invention are useful as antiinflammatory agents. They may be administered parenterally or orally in conventional pharmaceutical forms in the amounts of .100 to 1.5 grns. daily, preferably in divided does spread over 24 hours.

In order to illustrate the present invention, specific examples of the preparation of a number of compounds within the larger group of compounds encompassed by the present invention are set forth below:

EXAMPLE 1 Preparation of 3-(Benzamidomethyl) Pyrido (2.1-c)-s-Triaz0le Equi-molar quantities of Z-hydrazinopyridine and hippuric acid are heated from 140 C. to 190 C. during one hour. The reaction mixture is cooled and dissolved in 5% hydrochloric acid. The product is precipitated by addition of alkali and recrystallized from. isopropyl alcohol to give the pure product in 56% yield. It has a M.P. of 184186 C. Calculated weight percent for C H N O: C, 66.65; H, 4.79. Found: C, 66.93; H, 4.95.

EXAMPLE 2 Preparation of 3-(2-Benzamid0ethyl) Pyriao (2.1-c) -s-Triaz0le This is prepared in 74% yield using the method of Example 1 from Z hydrazinopyridine and N benzoyl-B- alanine. it has a M.P. of 180-l81.5 C. Calculated weight percent for C H N O: C, 67.65; H, 5.30. Found: C, 67.61; H, 5.18.

3,050,525 Patented Aug. 21, 1962 7 EXAMPLE 3 Preparation of 3-(Amin0methyl) Pyrido (2.1-c)-s- Triazole Dihydrochloride Is as Flollaws EXAMPLE 4 Preparation of 3-(Aminoethyl) Pyrido (2.1-c)-s- Triazole Dihydrochloride This is obtained by starting with the compound of Example 2 and carrying out the hydrolysisreaction of Example 3. The free base is obtained by the addition of alkali. The dihydrochloride melts at 254.5 C.

EXAMPLE 5 Preparation of 3-(2-Acetylamidoethyl) Pyrido (2 .1 -c) -s-Triaz0l e This is prepared by using the method of Examples 1 and 2 but using N-acetyl-fl-alanine instead of N-benzoyl- B-alanine.

What is claimed is:

1. A pyrido (2.1-c)-s-triazole having the formula:

wherein R is lower alkylene having from 1 .to 4 carbon atoms and R is selected from the group consisting of hydrogen, 'benzoyl and lower alkanoyl having up to 4 carbon atoms.

2. 3-(benzan1idomethyl) pyrido (2.1-c)-s-triazole.

3. 3-(2-lbenzamidoethyl) pyrido (2.1'c)-s-:triazole. 4. 3-(aminomethyl) pyrido (2.1-c)-s-triazole. 5. 3- (2-acetylamidoethyl) pyrido (2.1-c)-s-triazole. 6. 3-(aminoethy1) pyrido (2.1-c)-s-triazole.

References Cited in the file of this patent UNITED STATES PATENTS Bicking Dec. 15, 1959 OTHER REFERENCES Fargher et al.: J. Chem. Soc., vol. 107, pages 688-99 1915). 

1.A PYRIDO (2-1,")-S-TRIAZOLE HAVING THE FORMULA: 